March 20, 2025, 12:54 p.m.

How do you start out on the right track and stay there? Fail fast and learn quickly

All too often, projects fail big — major issues arise too late to do anything about them, and time and costs balloon. It doesn't have to be this way.

The Chief Delivery Officer's Newsletter

When starting out on something new, in virtually any arena, the urge to get on and do stuff is incredibly strong.

People playing Jenga as the tower falls down.
People playing Jenga as the tower falls down. Photo by Gustavo Fring on Pexels.

That’s pretty much the biggest error that can be made, especially with large projects.

Instead, you need to be guided by a vital principle:

Fail fast and learn quickly.

This heuristic is strongly related to the previous one, the most important principle — discover stuff first of all.

There’s two parts — fail fast and learn quickly. And neither is complete without the other. So what do they each mean?


This post is an excerpt from a page on The Chief Delivery Officer’s Handbook:

Heuristics for better project delivery leadership | Helios360

Fast and frugal rules of thumb to help project delivery start out on the right track and stay there


What does ‘fail fast’ actually mean?

It’s easy to have ideas. Some will be good. Some even very good. Others will be bad, and maybe even disastrous.

Experiments that fail are good experiments

Every project needs to build in a robust period of testing, trialing and experimenting.

With each of your experiments, get real users to use them, i.e. not yourself — you know how they work, you know how to get the ‘right’ outcome.

A desirable outcome from each experiment is failure.

You need to know when and where and how and why each of these things break. The earlier you achieve that failure, the better.

As a Chief Delivery Officer, it’s important to create a culture that is comfortable with failure. In fact, more than just comfortable, you should actually welcome failure.

Leaders must unequivocally give their teams permission to lean forward and take risks.

With one vital proviso — that you learn from it, and learn quickly.


What does ‘learn quickly’ actually mean?

Each failed experiment is a way not to do what you’re aiming to achieve.

That means learning, and where possible, learn quickly.

Analyse what went wrong and why, and work out what you can do about it.

Is it a fundamental problem? Or is it something that needs just some adjustments.

Learn those lessons, and bake them into a new set of experiments.


Do it while it’s cheap

Before you even start putting ‘spades in the ground’, you need to understand all that you can about the ways that the thing can go wrong to avoid discovering those by accident later on when failure becomes expensive.

If you spend 5%, 10%, 20% (or more!) of the whole budget on lots and lots of early experiments that unearth hidden problems and stop you from discovering those when you’re in the middle of building, you will potentially save 40%, 50%, 75%, 100% (or more!) increases to the overall spend that are necessary to accommodate these issues.

Make experiments that fail a requirement

No project should be given a green light if you don’t know in detail how if could go wrong and you have taken steps to avoid those problems.

Only when you have done that can you be confident that you will start out on the right track and stay there.


There's more delivery heuristics online in The Chief Delivery Officer's Handbook:

Heuristics for better project delivery leadership | Helios360

Fast and frugal rules of thumb to help project delivery start out on the right track and stay there


You just read issue #4 of The Chief Delivery Officer's Newsletter. You can also browse the full archives of this newsletter.

Share on LinkedIn Share via email Share on Bluesky
Bluesky LinkedIn Linktree Joe Baker @ Helios360
Powered by Buttondown, the easiest way to start and grow your newsletter.